If I was in your position I would look to air bnb or VRBO the property you purchase in San Diego this way you will have less negative cash flow than if you were to rent it out to a long term tenant. 

He put in a hot water heater, painted the upstairs walls white, put black shutters on the house, painted the deck grey, and painted the front door red.

I know in Orlando in most areas that don't allow air bnb, will allow you to have an air bnb as long as you live in one side of it while having it as an air bnb. 

It was a breath of fresh air. 

and seeking some wisdom for a rookie.Interested specifically in Kissimmee/Orlando/Davenport as Disney market feels familiar to me and it’s generally a cheaper entry point than beach condos.Looking at Regal Oaks (staying here now on vacation myself and enjoying it, though have read mixed things about occupancy), Windsor Hills, and Champions Gate.Goal is to have a second home that I AirBnb out the majority of the year but also can escape to when NYC is ruthless (like now :) hoping to live in the 150-250K range, bonus if there’s a pool (regal oaks has community pool and individual hot tubs), and solid amenities.Other than reading for my life, how can I number crunch and prepare for this?

Foreclosures, short sales, and off-market deals can provide these opportunities.Target up-and-coming neighborhoods with increasing home values rather than already hot areas.Research comparable recent sales and get an inspection to accurately estimate the after-repair value (ARV) before making an offer.Follow the 70% rule - the purchase price plus renovations should not exceed 70% of the ARV to leave room for profits after selling costs.Focus renovations on maximizing returns - kitchens, bathrooms, curb appeal rather than over-improving.Hire experienced contractors and have a project manager oversee work to keep things on schedule.Price the renovated home at or just slightly below comparable recent sales to facilitate a quick sale.

It seems from what I have been reading in regards to ADUs, the appraisers / LA market has not giving it the value it caution air quotes " deserves

**Air Conditioning:** The AC unit is malfunctioning.2.

Centennial allows them, but it's on the south side of Denver, and that's not quite as "hot" as the northwest and west sides of the metro area.

Posting too soon will just add more days to it being on market and when renovations are finished it won't be the "hot new" listing.